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Cheap MDW to OAK Flights

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Chicago to Oakland route information

Origin Airport Midway Intl.
Destination Airport Oakland Intl.
Airlines Serving Delta
Flight Price $331
Distance 1,840 mi



Cheap MDW to OAK Flights

  • Question : What airports do you fly into for Oakland?
    Answer : Chicago Midway International Airport is a wonderful airport, but there is a lower cost way to get to Oakland— O'Hare International Airport. It's just 16 miles away and flights are 48% cheaper over the next few months.
  • Question : Do some days of the week have more flight times than others?
    Answer : The day with the most departure times for this route is Wednesday with 10 options. However, with only six flight times, Thursday doesn't offer quite as many options when finding that perfect departure time.
  • Question : What is the cheapest day to fly?
    Answer : The cheapest day to fly from Chicago to Oakland is on Tuesday. If you want to save some cash on your next flight look for flights on Tuesday.
  • Question : What is the cheapest airline flying from Chicago to Oakland?
    Answer : Delta Air Lines is offering the best deal at $392. Better take a look fast because prices range all the way up to $2,175 over the next three months.
  • Question : Is there an alternative airport near Oakland?
    Answer : Metropolitan Oakland International Airport is a fine airport, but there is a cheaper option – San Francisco International Airport. It’s just 12 miles away and flights are being booked 31% cheaper over the coming two months.
  • Question : How long does it take to fly from Chicago to Oakland?
    Answer : If you are flying on Southwest Airlines, your flight will be just about four hours and 40 minutes (don't forget, there is a time change of two hours).
  • Question : How much is a plane ticket to Oakland (OAK) from Chicago (MDW)?
    Answer : Cost can range from $392 to $2,175, prices for MDW to OAK do change more than the majority of routes in the United States. The further out you book, the more likely you are to save.